Simply Enjoyable
by whimsicalwords
Summary: She could end these secret, purely physical interactions between the two of them at any time. She just didn't wish to at the moment; that was all. She was simply just enjoying herself…and Chuck. The relationship between Blair and Chuck progresses after the infamous night in his Limo in more ways and with more challenges than either of them had ever imagined.
1. Chapter 1

**Simply Enjoyable **

Blair sat at her vanity and observed her reflection in the mirror. Her gaze lingered a little longer than usual as she contemplated just how different the face staring back at her seemed. It had a certain kind of…glow. Of course, Blair did have a quick thought that such a replenished complexion was probably thanks to Chuck and the certain kind of pleasure he had been bestowing upon her lately. However, that thought vanished as quickly as it had arrived. Chuck Bass was absolutely disgusting, repulsive really, and the only reason she had even slept with him in the first place was clearly due to a momentary lapse in judgment. She could end these secret, purely physical interactions between the two of them at any time. She just didn't wish to at the moment; that was all. She was simply just enjoying herself…and Chuck. She glanced back into her mirror to see the rosy glow in her cheeks that the thought of Chuck had inspired and promptly groaned in response. Perhaps it was better to end this soon after all.

"Miss Blair, Mister Chuck for you," Blair quickly shifted her train of thought as Dorota called up the staircase.

She promptly jumped out of and pushed in the chair she had been sitting in, but stopped her sudden movements when she caught a glance of herself one last time. What was she hurrying for? It was only Chuck, and he wasn't even supposed to be here right now. Also, applying another coat of lip-gloss would probably be beneficiary. Not for Chuck, she just liked to look presentable. Besides, doing so would prolong the time it took for her to go greet him and she certainly didn't want to seem too eager.

Blair rummaged through her drawers to find her favorite, rather flattering lip-gloss and began to apply it.

"You know, I would enjoy those lips of yours any way," Chuck's voice whispered in her ear as his arms encircled her waist from behind. Why was he even there….and more importantly, for how long?

Blair didn't move for a moment but then quickly spun around to face him, "Why are you in my room?"

He smirked, "You've seemed to enjoy me in the location before…among others anyways."

She grimaced, "That's not what I meant."

"Ah, but you admit to enjoying it." He moved closer to her, "You know, it could be even more enjoyable right now."

She only rolled her eyes and pushed him away in response, "I don't have time for that right now, Chuck. Besides, you basically just intruded."

"That's not true at all, Dorota let me in."

"You know what I meant."

Chuck only moved even closer to her, repositioning his hands around her waist, their lips only centimeters away from actually touching, "I'm impatient, especially when I'm waiting for something as…as…enticing as you."

Blair knew the smart thing to do would be to pull away that instant and end the whole thing once and for all, but she delighted in the feel of the warmth of his breath as he tightened his grasp around her. She was going to reply, say something sarcastic, a witty remark in response but before she could he leaned down and kissed her. It was too late now, their lips danced a fiery tango and they somehow ended up landing on her bed to continue their intense make out session. Blair wrapped her legs around him and all Chuck could think about was how much he wanted her…in more than just the usual way he had ever wanted any girl.

**A/N: So…I haven't written a fanfiction in a really, really, really long time, but I felt compelled to write a Chuck and Blair one. It isn't too extraordinary, I know, but this was just to get started. I'm not sure whether I'm going to leave this one as it is or continue it, suggestions would be helpful. As always, any reviews and/or comments are appreciated. Thanks for reading! **


	2. Chapter 2

**Simply Enjoyable**

Blair felt perfectly content as her head lay on Chuck's chest with his arms draped loosely across her. That was exactly the problem. No matter how…how unbelievably perfect it may have felt in the moment…or many moments…it was only hormonal responses. Nothing more, nothing less. She was Blair Waldorf…and he was Chuck Bass.

She acted upon this realization quickly by sitting up straight in her bed, causing Chuck to shift his position and give her a look of bewilderment.

"You know, if you wanted to resume what we had been doing before, you could have just started from where you were," He only seemed to be half-joking.

She rolled her eyes, "No, it's not that. Not that at all." She bit her lip, "It's just…" Oh god, why was she even having a problem telling him this?

"Just what?" He seemed to be rather intrigued more than anything else, and his words actually held an undertone of…of…could it actually be concern?

Blair didn't dare glance back at him, "We have to end this."

He paused for a moment but quickly recovered, "But why, why would you ever want to end this…" he trailed off as he approached her from behind and began kissing the nape of her neck, a spot which had become a favorite of his.

Blair sighed, he certainly was convincing in his own way. "Chuck…"

She could practically feel his lips turn upward in amusement as he whispered in a purposefully seductive tone, "Blair…"

She turned to face him with the intent of letting him know she was being completely serious. However, he tactfully prevented her from doing any such thing by preoccupying her lips with other activities. In fact, he did so with such fervor that she almost forgot the issue she had been trying to address in the first place.

He pulled back away from her, "Is it even possible for you to still think we need to end this beautiful…?"

Blair glanced down, what exactly were they even? She hadn't felt the need to define them as anything before, but with the realization that Chuck couldn't finish his previous statement, she realized that she wouldn't have been able to either. They couldn't really properly claim to be anything…or nothing.

"This beautiful what?"

"…this beautiful, incredibly detectible series of interactions we have established."

She rolled her eyes, "Please, is that the best definition you could come up with? I thought Chuck Bass was infamous for his lines with women."

He looked into her eyes, "But you're different, you make me…at a loss for words."

"Exhibit A," she retorted.

He couldn't help but briefly flash a real smile, but it disappeared as he said, "Well, if you want some other kind of definition, maybe you shouldn't be so worried about Nate."

Blair felt a sinking feeling in her stomach. It was true, she was worried about Nate. Admittedly, Nate had never made her feel the way that Chuck did but they had still dated…for a really long time nonetheless. Not only that, but Chuck was his best friend and she had slept with him literally less than a few hours after she and Nate had broken up. What kind of person did that even make her? Certainly not the Blair Waldorf she was expected to be.

She realized she had been getting lost in her thoughts, "Don't act like I'm the only one here who is worried about what Nate is going to think."

"Listen, Nathaniel and I are best friends, true, but I'm also sure he would come to forgive me. You guys had broken up at the time, and besides, I'm willing to risk Nate finding out if it means I get to spend more time with you," He pushed a loose strand of her hair behind her ear.

"And by that, you mean in my bedroom."

"Hey, that's unfair; you certainly know well enough I'm capable of performing in varied locations. Perhaps the back of a limo rings a certain bell?"

She grabbed a pillow lying nearby and threw it at him, "You're disgusting."

Chuck, however, did notice a certain look he had never seen in Blair's eyes before, "Listen, I was only kidding. You know how I feel about you, that I actually do…"

"Do what?"

"I was about to finish, if you will just give me a chance, sweetheart," the addition of the pet name was certainly not intended to be endearing, "As I was saying, I do like you and you know that. …I like you a lot, and not just for what you think. It may be easier to keep this whole thing a secret, I understand that, but I'd be willing to expose such details if it meant getting to have you all to myself."

Blair bit her bottom lip, she knew how she wanted to respond, but she also knew that was a completely different response than the one she should have offered.

"Miss Blair, Mister Nate for you," Perhaps the response would just have to wait until later.

**A/N: Thank you so incredibly much to everyone who reviewed the first chapter, it certainly made my day and my first experience returning to fanfiction after a long departure well worthwhile. I've decided to continue this at the request of a few of you. I hope it continually becomes better; I'm still getting back into the hang of this whole fanfiction thing. Not to mention the fact that this is my first Gossip Girl fanfiction ever, so bear with me. **

**As always, any suggestions and/or comments are much appreciated! Thank you for reading!**


	3. Chapter 3

**Simply Enjoyable**

Blair bounded down her staircase. What was Nate even doing at her house? It had been made pretty clear from their last encounters that he had more important things to be worrying about than her. Although Blair had been crushed that he didn't want her by his side just a few weeks ago, she couldn't help but feel that perhaps their break up had been for the best after all. Of course, that didn't excuse her actions of being so quick to jump into Chuck Bass's arms…or rather the back of his limo. Her face drained as she gave a smile to Nate and realized that Chuck was still in her bedroom. If he even thought about coming out, she would literally kill him.

"Blair…" He nodded at her and gave a subtle smile.

She forced a smile back, "Nate, what are you even doing here?"

He sighed, "Oh you know, I was just in the neighborhood," she stopped him mid-sentence by giving him a look that indicated they both knew how ridiculous such an excuse was "Okay, so, it's just…,"

"Just what, Nate?"

"Okay, I know you're probably still really mad at me about…well, about everything, and I completely get that…it's just, Blair, I…I…"

He had piqued her interest, "Say it already."

"…I miss you."

Blair wished she could say the same back, but the truth was that she had missed Nate momentarily but that those thoughts had vanished and been replaced by thoughts of…dare she even think it…Chuck Bass. "Well, of course, I mean that's natural with a recent break up and all. Nothing to be worried about Nate, dear."

His eyebrows furrowed, "Well…I mean, I guess I thought that maybe you might have missed me too. Even just a little bit?"

She sighed, "Nate, of course I missed you. It's just that such feelings will not benefit either of us. You have a lot to be worrying about right now and you've already proven that you didn't want me to be the one by your side for it all, so..."

He shoved his hands in his pocket, "Blair, I didn't know what I was doing. I didn't know how much…"

She couldn't help but roll her eyes, Blair Waldorf was not that easily taken back, "How much you'd actually miss me? That I was actually worth something?" She didn't even know why she was becoming angry; Nate hadn't even really said anything.

He did look genuinely sorry though, "Blair…I…I…"

She quickly cut in, "I'm sorry, I know you have had a lot going on. I just think it's better if we…," she looked off to the distance, "stay friends right now. We could do that, friends, right?"

He offered a genuine smile in response, "Sure, friends," And then he added, "And as friends, would you want to go to dinner tomorrow night with me?"

She couldn't help but agree, "Of course," but she quickly made sure to add, "As friends only though."

"Right, of course, as friends," and with that Nate left.

Blair sighed and pondered if it was even possible for things to become more skewed. She quickly realized that Chuck was still in her bedroom, and confirmed that it indeed was. She began to race up the stairs; god only knows what he might have done in there with her gone so long. However, she found him waiting at the top of the staircase behind the wall rather than in her bedroom.

"Quite an interesting conversation you had with Nathaniel."

"…were you eavesdropping on us?"

He raised his eyebrows, "Quite the contrary, I just happened to be passing by and couldn't help but overhear."

She pushed him, "Well, then you should know that we just agreed to only be friends."

"Right, and I assume the best way to do that is with romantic dinner plans."

She quickly retorted, "Nate is just naturally a gentleman," and then she rethought her statement, "and besides, there is nothing romantic about our plans."

"Yeah, well, not yet anyways," Chuck glanced off.

Blair, to Chuck's surprise, began to laugh, "What? Don't tell me you're jealous."

"No. I don't get jealous."

"Good, fine, that's just great, then I guess you won't mind me calling Nate to ask him right now if he'd like to come back over because I've just been," she trailed off and purposefully began with a dreamily seductive tone, "ever so lonely lately."

Chuck clenched his teeth, "First of all, we both know that's not true," He pulled her closer to him, "Secondly, if you would have let me finish, I was about to say that I'm not jealous of you and Nathaniel because I know for a fact that you two will never have what we have."

"What do you even mean, Chuck? We don't have anything."

"Oh, but we do, Blair," he pulled her dangerously close and whispered in her ear, "We have chemistry…" he began to kiss her neck and she let out a sigh of pleasure, "and the kind of physical enjoyment that Nathaniel will never be able to bring to you," he continued kissing her, "and we have the fact that we're…we're inevitable."

She turned on her heels to face him, "What does that even mean, Chuck?"

He challenged her, "I'm still waiting for you to tell me."

**A/N: Thank you so much for all the reviews! It means a lot! I'm trying to update as quickly as possible for all of you. I'm not quite sure where this story is headed yet, but hopefully it will be towards some better writing, I haven't been too pleased with myself yet. **

**As always, any suggestions and/or comments are much appreciated. Please review, lovelies! Thank you so much for reading.**


	4. Chapter 4

Blair Waldorf never felt weak. She never felt afraid to say what she wanted. She especially had never cared what Chuck Bass thought of her. However, at the moment Chuck had asked her what they were, she felt all of those things and more. Not only that, but she wanted to crawl into a corner and hide from it all. This wasn't supposed to happen; not to her; not to Blair Waldorf.

She glanced up and he was still looking at her…waiting, "Well, are you going to say anything?"

"Chuck…"

He gave a smile and a roll of his eyes after her pause had been extended too far for his liking, "Right, well I should have known you would crawl back into Nate's arms. That is the proper Blair thing to do after all." He scoffed, "Oh, and when you two don't work out again, you know where to find the back of my limo."

Who did Chuck think he was? What made him think he was entitled to even make such comments? Blair grabbed his shoulder before he could finish turning away, "I never even said anything about Nate. Maybe that's what you think the Blair thing to do would be, but that's no different from Chuck Bass leaving so easily."

He turned to face her again, "Don't say that when you know exactly what to say to make me stay."

She winced, "Why should I even say anything when you've only implied what you feel for me? How do I even know that…"

"Know what?"

"Let me finish," she sighed, "That I even mean anything to you?"

He noticed the way that she looked toward the ground as she finished her inquiry and he couldn't help but melt into her. God, why did this girl have such a power over him? He was supposed to be Chuck Bass; he was supposed to be the kind of guy no girl could ever sway and yet here he was in Blair Waldorf's house trying to comfort her and not because he wanted some kind of sexual favor…but because he actually…liked her.

"Blair, listen to me, you do mean something to me and you know that it could never be easy for me to turn away from you…especially not now. You mean…," he paused, debating whether he should even continue, and noticed the look of hurt was still somewhat noticeable across her features, to hell with it, "You mean more than anybody has ever meant to me before."

The look vanished and her eyes lit up, "Chuck…I…I mean, it's just that, you mean that to me too."

He chuckled, "Well good, I'm glad that's settled. Now…," he trailed off and swept a piece of hair out of her face before inviting her into a passionate kiss.

She had to force herself to pull away, "I do have to go though, my mother is expecting me to be present for a dinner, something about one of her designers…"

"Well, I could always accompany you, and I'm sure we'd have time beforehand to…," he began planting kisses on her neck, "to finish what we started earlier."

Blair sighed because she didn't want him to stop, but she knew that she had to tell him to, she was already worried about what Nate was going to think let alone her mother, "Chuck, don't be silly, we haven't told anybody yet…about any of this. We only just realized ourselves that this is even anything at all."

"What? You don't think I'm worthy of meeting your mother?"

"No, no it's not that…," she trailed off, "Okay, well come on Chuck, I mean you're Chuck Bass, you don't exactly have the best reputation."

"As opposed to the real Blair Waldorf who I'm sure at least somebody besides me would recognize, perhaps your mother."

She lightly pushed him, "I'd just rather wait. I mean…we should test the waters before we dive into the deep end is all."

He nodded not in agreement, but rather in consent, "If that's what will make you happy, but you might have to make it up to me someway tomorrow…"

She giggled as he drew her into him, "Is that so?" She looked up into his eyes and then put everything she had into kissing him, "Something to look forward to."

**A/N: Thank you so much once again to everyone who has reviewed the previous chapters! This one isn't my favorite chapter so far, but hopefully as the story develops, there will be more interesting, slightly longer chapters to come. **

**As always, any comments and/or suggestions are highly appreciated. Thanks for reading! **


	5. Chapter 5

**Simply Enjoyable**

Blair actually felt nervous as she sat across the table from Serena at breakfast. However, she wasn't nervous because she felt insecure beside the leggy, carefree blonde next to her but rather because of what she was about to tell her…that she actually liked Chuck…and that there was something between them. Not only did she have to tell her best friend that something more had happened besides the time in his limo and the time at her 17th birthday party, but that she actually wanted to continue to be involved with Chuck Bass. Even she knew that such a statement was unthinkable to say aloud.

That didn't stop her though as she blurted out, "Serena, I have something to tell you."

The blonde politely smiled back, "What is it, B?"

She felt her stomach twist, "Oh god…," she couldn't believe she was even saying it, "I can't believe I'm even saying this but I think that I might actually like Chuck."

Serena only laughed, "Well of course, I mean the time I saw you guys at your birthday party you two didn't exactly look completely platonic."

Blair rolled her eyes, "Wait, so you don't think it's completely terrible that I like him?"

"B, of course he's not exactly my first choice for my best friend, but if you two make each other happy, then I support you," she flashed a genuine smile.

Blair smiled back and jokingly replied, "Great, does that mean that I actually have to support you and Humphrey now? You know, you could do so much better, S."

"This coming from a girl who's dating Chuck Bass?"

Blair's eyes widened, "Whoever said anything about me dating Chuck Bass?"

Serena gave her a confused look, "Well…I mean, you kind of just did."

Blair look appalled, "I said no such thing. All I said was that I liked him."

"Right, but I mean you two dating just kind of seems like the next natural step. Unless you two just want to like each other in private and do whatever it is you do…oh god, I really don't want to picture what it is you two do," Serena mockingly covered her eyes in disgust as if doing so would block images from her mind.

"Our sex life does happen to be quite incredible, but that's beside the point," Blair laughed only to become serious, "I mean, I'm sure we would date…if we wanted to. It's just that, we haven't really talked about 'dating' exactly yet."

Serena shrugged, "Well you might want to soon if you're actually serious about this, B. Chuck Bass hasn't exactly been known for staying faithful."

Blair sighed because she knew that what Serena said was true. What if Chuck was off with some other girl right now and she was just stupid enough to believe that he actually cared about her? Her cheeks flushed at the thought; she would murder him with her bare hands. She relaxed a little when she realized that such thoughts were only assumptions but decided to go find him nonetheless.

"Well, this has been great S, but I have to go," Blair quickly pushed in her chair and threw some money out of her purse onto the table, "Busy day, you know, important things to take care of."

Serena amusedly watched her best friend hurry off and called out knowingly, "Good luck with Chuck."

Blair arrived at Chuck's hotel to find him in his trademark silk pajamas, robe, and with a look of tired surprise spread across his face, "Isn't it a little early, Waldorf?"

She disregarded his statement, "I was at breakfast with Serena and an important matter came up."

Chuck snorted, "Listen, as interesting as I find your friend's struggles with Dan Humphrey, I'd much rather wake up to something else," he looked over her attire suggestively and added, "Perhaps something in a yellow sundress."

She only rolled her eyes, "You think I would actually come to tell you about something involving Humphrey? I can barely stand to listen to that myself."

"Then what is it?"

She trailed off, "It's just that Serena said something after I told her about us…and it kind of actually made sense."

"Well, what did she say?"

She sighed, "She asked if we were dating, and I said that we weren't but really I don't even know. Then she just said that I better define us as something soon because 'Chuck Bass isn't exactly known for being faithful' and I realized it was true," she continued speeding up her words more and more, "Then I had this image of you in bed with some disgusting tramp and the thought that what if I was just some other girl to you and what if I was just incredibly stupid and what if…,"

He cut her off, "Blair, I would never do that to you. I could never. Besides, nobody could ever compare to…the standards you've set."

She smiled for a moment, but it faded, "But I mean, there's still nothing stopping you from doing anything like that."

He paused for a moment, "Besides the fact that I would never want to hurt you? Blair, what do you want me to say? That we should be boyfriend and girlfriend," he chuckled as if the thought was the most ridiculous thing he had ever heard, "You couldn't possibly want that." As he said those words though, he realized that whether or not she did, he wanted that. Chuck Bass wanted to be a boyfriend. What had the world come to?

All Blair heard were the last five words though and she quickly turned to grab her purse off his counter to hide the look of disappointment on her face, "Of course not…just forget I said anything." She added through clenched teeth, "Goodbye, Chuck."

Chuck opened his mouth to say something; anything to make her stay but no words came out. He just stood there and watched her slam his door shut and he had never felt worse in his entire life. Blair actually wanted something more? Blair Waldorf actually wanted to claim to be his girlfriend? That was perhaps even more shocking than him actually wanting to be in a committed relationship at all. Yet here he was doing nothing as she was leaving. He would fix this though, right away, and he smirked as his plan formulated in his mind.

**A/N: As always, a big thanks goes out to everyone who reviewed the last chapters. I don't quite have anything else to say except for that. **

**As always, any comments and/or suggestions are highly appreciated! Thanks for reading, dears! **


	6. Chapter 6

**Simply Enjoyable **

Chuck Bass stared at the flowers, pink peonies to be more specific, that were lying on his bed. How did it even get to this point? How did he even get to this point? He was supposed to be Chuck Bass: billionaire playboy not Chuck Bass: the guy who wants to settle down with Blair Waldorf. The last time he had checked that had been Nate's job description. However, things certainly had changed. A smile spread itself across his face as his thoughts drifted back to the time in his limo, and the time that had changed everything was the only thought he needed to decide to go through with his plan to make Blair his and only his.

A knock on the door interrupted him, "Going out so early?"

He looked at his doorway to find Serena staring, with some hint of disapproval, "Not quite."

Her gaze drifted to the peonies neatly placed atop his comforter, recognizing her best friend's favorite flowers, "Are those for Blair?"

He gave her a smirk as he grabbed the flowers and brushed past her out his door, "Perhaps."

Serena only let out a deep breath as she watched Chuck Bass walk away, pink peonies in hand, to try to win over Blair. She certainly never thought she would live to see the day when any of that would happen.

Chuck told Arthur to take the long way to Blair's, and he didn't quite know why. He wasn't nervous, Chuck Bass didn't get nervous, and especially not when it came to women. He leaned back into his seat though as he realized that the whole point was that Blair was different. She was incredible.

He stepped out of the limo, flowers in hand and began to walk towards Blair's doorway. He stole a quick glance at her window only to happen to catch the sight of two silhouettes standing surprisingly close to one another. His eyebrows furrowed at the image, it was probably only a coincidence. He continued approaching to the doorstep and was promptly greeted by Dorota.

"Miss Blair not here, Mr. Chuck."

He scoffed, "Listen Dorota, I happen to know she's here."

Dorota looked helpless for a fleeting moment, "Mr. Chuck, I try to tell you, Blair is not here."

Chuck nodded, but only as a notion that he was prepared to accept any challenge, "That's fine then, I'll just wait for her."

Dorota looked bewildered as Chuck brushed past her as he muttered a quick 'excuse me' under his breath. It only took her two seconds afterward to begin hurrying up to Blair's room and one second after that to realize that Chuck was running after her. They were both now engaged in a race to her room. However, Chuck easily surpassed her and flung open the bedroom door only to find Blair and Nate sitting on her bed laughing and Kleenexes in the trashcan nearby. Nate had been there to comfort her for something he had done. The whole thing felt too familiar, perhaps because that was how they had begun.

Blair glanced up startled to find Chuck standing there, and only then did she realize how things looked, "Chuck…what are you doing here?"

He didn't know what to say, "I don't know anymore." A single pink peony drifted down from the bouquet of flowers he was holding behind his back and Blair happened to see it. She wanted to run into his arms, tell him that everything was forgiven, but she couldn't shake the thought of what he had said earlier.

"Chuck, you literally told me only a few hours ago that we could never actually be together. This doesn't make any sense."

"I didn't realize what I was saying, that you would actually even want to be with me." He added on hastily, "It didn't take you long to run back into Nathaniel's arms though."

Nate, now awkwardly standing a corner, spoke up, "Hey man, it's not like that. We didn't do anything. In fact, I was just giving her advice about you."

Chuck rolled his eyes, "Right, I'm sure your intentions were pure."

"Blair glanced from Chuck to Nate and from Nate to Chuck and back again, "Just stop," she addressed Nate first, "I'm sorry, thanks for being here for me, but I need to talk to Chuck alone now."

"No worries, I was just leaving," he patted her on the shoulder on the way out and she winced.

She turned her attention towards Chuck, "I don't understand. What do you want, Chuck?"

A/N: I was planning to make this a longer chapter, however, I didn't have quite a lot of time to work on the chapter for today but still wanted to stick to my routine of updating this story everyday. I promise a longer chapter will be coming soon though, and I'll attempt to make it of better caliber than normal! Thank you to everyone who has been reviewing, it means a lot.

As always, any comments and/or suggestions are appreciated! Thanks for reading.

p.s.: I didn't go back over this and spellcheck/edit and stuff…sorry for any stupid mistakes…it's like 1 in the morning where I'm at.


	7. Chapter 7

**Simply Enjoyable **

Chuck just stood there and stared at her for a moment. If he were to be completely honest, the truth was that she had every right to ask what she had of him. What did he want? He had thought he knew indefinitely before he found her with Nate so easily. The fact that she had been with Nate wasn't what bothered him the most though, it was the fact that he considered it a possibility that he would never be good enough for her and Nate having been the one there to comfort her only reaffirmed such beliefs. He stood there a moment longer though and looked at her for a moment more and he realized that he couldn't just let a good plan go to waste.

Blair, however, was beginning to look progressively more annoyed at the situation, "Are you going to say anything or just stand there?"

He nodded at her, "Right," he trailed off, "First, I just wanted to apologize for what I had said earlier. I do want you."

She quickly muttered, "Not like I want you."

He stepped closer and cupped her chin in his hand to guide her eyes upward to his, "You're right, Blair. However, it's only because I want you so much that I doubt anybody has ever wanted anything more. You're all I think about, I can't sleep, I can't eat, it consumes me but all of that is worth it because you're incredible. I really mean it, when I say that I don't just want you, but that I want to be with you," he realized he was still holding the peonies behind his back, "and that's what I came here to tell you."

She gave him a soft smile, but slightly shook her head, "Then why you couldn't you just tell me all of that earlier?"

He sighed, "I guess I was just afraid that unlike most of the women in the world, you wouldn't want to be with Chuck Bass."

She laughed, "Chuck, don't you know how I feel about you? I want you so much it hurts…I mean, I want to be with you."

"Well, I'm certainly glad to hear that, Miss Waldorf. Would you care to officially go on a date with me tomorrow night?"

"I couldn't think of any way better to spend tomorrow evening, Mr. Bass."

Chuck felt like he never had before as he swept Blair off her feet, both figuratively and literally, though he was only fully aware of the latter. He spun her around the room and landed her in an embrace which led to a kiss.

"Although our official date may be tomorrow evening, I can think of a couple of other enjoyable ways to spend tonight."

Blair returned his suggestive look with a seductive smile and pulled him onto her bed, "You'll have to elaborate on that. I'm dying to know your suggestions."

**A/N: Okay, so this wasn't a long chapter either. However, I promise that the next one will be considerably longer than the others have been! Although, I will be leaving for a week tomorrow and I am uncertain if I will have internet access at my destination. I will do my best to keep this updated, otherwise I will continue it next Saturday! **

**As always, any comments and/or suggestions are highly appreciated! Thanks for reading!**


	8. Chapter 8

**Simply Enjoyable**

Chuck Bass noticed that a genuine smile, not a seductive grin intended to invite a woman to stay a little longer, not a smirk that had just the right touch of superiority to win over business deals, not even the small upturned corners of his mouth that indicated he was pleasantly surprised, but it was a completely natural smile that found its way onto Chuck's face at the moment he stepped into his limo after kissing Blair goodbye. This was a big deal, because Chuck Bass may have been known for his seductive tendencies or his persuasion to potentials, but Chuck Bass had never been known for being the kind of happy he was right now…not to anyone else or even to himself. However, right now, the smile that exposed the tiny gap between his teeth and reflected the twinkle in his eye made him not care about any of that.

He practically galloped into his suite, only when he realized that Nate was waiting there for him, did he properly revert back to the proper Chuck Bass manner, "Nathaniel."

"Chuck."

"Would you care to explain why you broke and enter into my place of living?"

Nate rolled his eyes, "It's not breaking and entering when you're the one who gave me a key."

Chuck's raised eyebrows began to lower themselves, "Right, I guess I forgot about that matter. Anyways, I assume you came here for a certain reason?"

"Alright, let me just come out and say it. Chuck, I don't want you to hurt Blair."

He scoffed, "As opposed to what you did to her?"

"That was different. Listen Chuck, I know I did some pretty messed up things to her, but at least I knew when to end it."

"Nathaniel, stop deluding yourself, she ended it when she left you and came to my club and slept with me that night," only after it was said did Chuck realize the subject he brought up.

That was all Nate needed, or wanted to hear, "I'm done. You can be a jack-ass friend to me all you want, but if you so much as pull your crap with Blair, you'll hear from me." He started to walk out the door.

Chuck grimaced, but he managed to be the bigger person for the first time in a long time, "Nate, wait," his friend turned back, "Listen, I know why you think that I would do something to her; something like I've done before, but I'm telling you that I've changed now; she's changed me. She's…"

"What, Chuck? You expect me to believe any of that?"

"Yes, because unlike you, I see Blair for who she really is and I appreciate that," he didn't stop himself, "No…I love that. I LOVE her."

With that the twisted look of disgust and distrust disappeared from Nate's face, "I didn't know you felt that serious about her."

"Well, I do," he added on hesitantly, "and I swear to you I would never do anything."

Nate gave a light smile, "Alright, well, just don't go back on your word, buddy," he patted his best friend on the shoulder and left.

Even though things still weren't completely resolved between the two of them, their old friendship finally had hope of resurfacing again. Now all Chuck had to worry about was how to make his first official date with Blair everything she wanted and more and as they both knew, she was not an easy one to please…in many ways. However, Chuck Bass was one to always like a challenge. It kept things interesting.

Later that evening, Chuck found himself sprawled out across his leather couch, scotch in hand, watching Audrey Hepburn movies for inspiration. He didn't know whether to be proud or ashamed of the extent of the effort he was putting into making a magical first date for Blair. He was on Breakfast at Tiffany's when his doorbell rang. He panicked, quickly shut off the TV, and cursed. What was he doing?

Although when he opened the door and found it was Blair, clad in a silky black dress and heels nonetheless, he couldn't help but notice the fluttering feeling in his stomach, "Blair, I didn't expect to see you hear so late."

"Why? Don't you like surprises," she winked and gave him a wicked smile.

He raised his eyebrows, "Don't tease me now."

She pouted with fake innocence and cupped his chin in her hand, "Now, would I ever do that to you?"

"Perhaps."

She only laughed in response, but all he could do now was contemplate the kind of lingerie she was wearing under the thin sheet of black silk, "Blair…"

"Yes, Chuck?" she had gone to his counter and was pouring herself a drink. God, he loved her when she wasn't afraid to just do what she wanted.

He snuck up behind her, "We both know you must have come here for some reason," then he leaned in closer and whispered in her ear, "So why don't you tell me?"

That wicked smile returned, "Maybe I just like you."

"Imagine that," he planted a kiss on the top of her forehead.

Then she stood on her tiptoes and leaned into his chest and muttered, "You missed the part where you're supposed to say how much more you like me."

He smiled attentively, "Of course, I was about to add that nobody could possibly like anyone or anything more than I adore you," he looked into her eyes and meant every word he said, "You, my dear, are exquisite," then he added reluctantly, "which is why whatever you had planned will have to wait for tomorrow night. I can't have you showing up my plans."

She pouted, "How do you even know I had anything planned."

"Because I _know_ you."

She gave a subtle smile, "Can we at least cuddle?"

He wrapped his arms around her, "Gladly."

She laughed and he loved the sound of it, "I never thought I'd see the day when Chuck Bass wanted to _cuddle._" He only smiled.

**A/N: Good news! There is wifi at my current location! I will try my best to continue updating, although this story is soon coming to its close. This is a slightly longer chapter indeed than certain previous one, although I will try to at least making the final chapter of this a considerable word count. Thank you for all your support and reviews thus far! **

**As always, any comment and/or suggestions are highly appreciated! Thanks for reading, lovelies!**


	9. Chapter 9

**Simply Enjoyable **

Chuck rubbed his eyes and let out a yawn as the sunlight began to peer through his bedroom window. He glanced downward to find Blair still curled up next to him and her eyes sweetly closed. She looked so innocent, and it was so natural. He smiled at the sight; it was quite a deceiving look for her. Then his thoughts turned to the fact that he was waking up in bed with a woman who he hadn't had sex with…or at least tried to seduce and gotten something in return. He couldn't remember the last time that had happened, actually, if it had ever happened. He really did care about her, maybe he even loved her. He quickly closed that last part out of his mind. Chuck Bass didn't love anything except for money and women and the things both of them gave him.

Blair squinted her eyes and caught Chuck still staring at her, "How long have you been awake?" She still sounded tired even though they had actually gotten sleep for once.

"Not that long," he leaned down to kiss the top of her head, "But you are going to have to leave."

Her eyes widened, almost into an accusatory glare, "I'm not just one of your whores you can kick out. I'm actually of value."

"Which is exactly why you're going to have to leave," he smirked.

"What are you even talking about?"

He smirked, "I'm talking about the fact that we have our first date together tonight and that such an event for such a _valuable_ woman as yourself requires my undivided attention," then he kissed her, "and you have proven yourself in the past to be a distraction."

Her face lit up, "Chuck, you don't have to do all of that."

"Please, Waldorf, we both know that I do."

She laughed, not denying the fact, "I'm looking forward to it, who knew you could actually be romantic?" then that wicked smile from the night before managed to make a reappearance, "and don't forget about those plans you said I would have to wait until tonight for."

"How could I?" He watched her as she shimmied back into her dress and took a glance in his mirror, her eyes registering some disappointment.

As she walked out, he called after her, "You look beautiful." She looked back over her shoulder and gave a deliberately exaggerated roll of the eyes before closing his door. He flopped back onto his bed, just to think about how surreal it all was for a moment.

However, he quickly recovered from the position, and began to get dressed. It was time to get down to business. The truth was that he didn't just want, or need, to prove to Blair that he was worthy of having her but that he also needed to prove it to himself, though he certainly would never admit such a thing aloud. He refastened his bow-tie around his neck and ran a hand through his hair before he left.

Chuck stepped into his limo, "We have a long day ahead of us, Arthur."

Arthur looked into his rearview mirror to make eye contact, "Yes, Mr. Chuck. It is my pleasure."

"To the usual florist and candy store, then I also need to pick up a very important piece of jewelry as you know. Oh, and later Arthur, the reservations are for the Lion Den."

"Mr. Bass, I thought the restaurant was not open to the public yet?"

He smirked, "Oh, it's not. I just happen to know some people."

Arthur shook his head as the window that separated them went up.

The first stop was the florist. Chuck bought a large bouquet of pink peonies and also had a large beautiful arrangement of the flowers sent to Blair, along with a note on his usual stationery that read, "Can't wait to see you tonight. You are perfection." Short, sweet, and very much to the point.

The florist asked him for his name as he paid, "I'm Chuck Bass." He could have sworn he saw her have a mild stroke; it wasn't because she was surprised to see him though. He had done business with her in the past; it was only the first time that he had actually come in to pick anything up.

She patted his hand as he left her shop, "Good luck, Mr. Bass."

He couldn't help but smile, "Thank you, I do suppose I may need it."

The next stop was Blair's favorite candy store in the city. He intended to pick up her favorite bonbons, chocolates, and of course macaroons. He watched as the cashier carefully wrapped the boxes in bows to make sure that everything was done to perfection. This was certainly not the time or place for mediocrity. He was satisfied as he handed over the money and left, making record time.

The final stop was a large jeweler, where he had reserved the new, diamond bracelet that was supposed to accompany the Erickson Beamon necklace he had previously gifted her for her 17th birthday. That transaction also went smoothly as he delighted in the envy apparent on the faces of the others in the store who couldn't help but to watch his purchase.

His plan now had all the items it required; it was up to only him to make it successful now. Surprisingly, he felt a little nervous…even a little shaky. However, he only blamed it on a supposed lack of sleep from the night before. The time had quickly come and gone and he once again lowered the window between himself and Arthur to give him the go ahead to Blair's, where he would pick her up…and hopefully never have to let her go if his all-encompassing plan lived up to it's potential. He couldn't believe he was doing this.

**A/N: So…the next chapter shall be the last chapter of this story! I shall make it exceedingly longer and attempt to satisfy all of you lovely readers needs and wants with it regarding this story. I am still so incredibly happy for any and all of the support that has been given for this, especially since this was my first piece after a considerably long departure from fanfiction. **

**As always, any suggestions and/or comments are highly appreciated! Thanks for reading!**


	10. Chapter 10

**Simply Enjoyable **

Blair walked over to the mirror to observe herself; she looked simple yet elegant in her plain dark red dress. Her hair cascaded in brunette waves, bouncing lightly on her shoulders and suggesting that perhaps she wasn't quite as serious as her attire suggested. However, both the diamond encrusted headband and Erickson Beamon necklace that she dawned reflected a certain kind of prestige that only made her seem more untouchable. Her outfit, to say the least, was incredibly compelling and she smiled subtly because she recognized this as a great success. Of course, having a fashion designer mother probably had helped her somewhere along the way.

She walked confidently in her heels over to the window and peeked out just in time to see Chuck's limo pulling up, "Pull it together, Waldorf," she muttered to herself as she realized she had actually become nervous at the sight. She prided herself on the ability to maintain a cool exterior.

She heard the doorbell ring and then Dorota call up the staircase, "Miss Blair, Mr. Chuck for you."

"Coming, Dorota," she called back, as confidently as she could even though the truth was that she was incredibly excited. She felt special, not because she had never been taken on an extravagant date before (She had dated Nathaniel Archibald after all), but because Chuck Bass was the one making it happen.

She glided down the staircase effortlessly and she noticed that Chuck's mouth stood agape for a few seconds as he made no effort to hide the fact that he was observing her in every way possible. She didn't squirm or feel uncomfortable at such an act, she only returned the favor as her subtle smile became slightly more provocative and amused. This was exactly what made them great for one another. She reached the bottom, and he nodded.

"You look beautiful," He interlocked his arm with hers to escort her to the limo and gave a gesture of departure to Dorota, who looked even more amused than Blair had previously.

"So, are you going to tell me your plans yet," Blair smiled and Chuck only shook his head.

"Quite the contrary, it will just have to be a surprise," He opened the limo door and stepped in after she had seated herself.

She pouted, "You know how I hate surprises though."

"Perhaps that's only because you've never known what a good surprise is."

"Perhaps that's because all surprises are bad."

He chuckled, "I promise this one won't be."

She rolled her eyes, "I'm trusting you."

Even though she was only kidding, both of them shifted uncomfortably. A lot had happened between them in a very short amount of time, yet neither had ever claimed to trust the other. Was it because they didn't or because they couldn't? Simultaneously, without knowing, they both pushed the thought out of their mind and smiled at one another as they toasted glasses of champagne.

The limo rolled to a stop and Arthur announced, "First stop, Lion's Den."

Blair squinted, "That can't possibly right, and that restaurant isn't even open yet."

"For you, it can be," Chuck raised his eyebrows and stepped out of the car to open the door for her.

She looked up at the exquisite building, "I must admit, I'm already impressed."

"You're only satisfied, not impressed," He wrapped an arm around her shoulder and quickly added, "But don't worry, by the time the night's over, you'll be enthralled."

"In that case, I guess I'll have to return the favor later," She winked and sped a little farther ahead. God, she was breath-taking.

They sat down at the restaurant and ordered their food. The seating overlooked the New York skyline, the food was delectable, and the service was lovely. It was a perfect choice for a first date, classic maybe, but also unexpected coming from Chuck Bass. They engaged in their usual conversation and banter for a while but then Chuck noticed Blair staring down at her plate, as if she was contemplating whether to say something or not. Was the date not good enough? He should have known…

"Blair, what's wrong?"

She quickly looked up as if she had just been awoken from a dream, "Oh nothing, really, this is all lovely. It's so perfect."

He knew better than to believe her, "Don't lie to me, Waldorf."

"I'm not lying, Chuck. This really is perfect already."

"Alright, then what is wrong?"

She sighed, "It's dumb, nothing to worry about. I was just thinking."

"Tell me; perhaps I can relieve some of your troubles."

She smiled slightly at his over empathetic gaze, "It's just that…well, do you even trust me?"

He paused and she noticed, "It's okay if you don't."

He thought about it a little longer, "It's not that I don't trust you, it's that honestly, I'm terrified of losing you and that I know you don't trust me either. I'll admit, trustworthiness isn't my strong suit, but I still want more than anything for you to trust me in order for me to trust you completely."

She looked down, "Is all this a mistake then? I mean, we can't even completely trust each other?"

This wasn't exactly how he thought the date was going to go, "Blair, I… care about you a lot and I'd be willing to completely trust you if you were willing to completely trust me, even though I understand that's a huge leap…for both of us. Let's be honest though, would either of us be willing to give up everything here only because we couldn't trust each other?"

"Well, maybe not…"

He didn't hesitate, "I trust you, Blair."

She looked up, "I trust you too."

He took her hands in his, "You don't know how much that means to me," and he leaned in to kiss her.

The rest of the dinner went much more smoothly, and Chuck certainly was glad that his plan hadn't spiraled into disaster yet after all. They walked back to the limo and as Blair sat down, he handed her the assortments of her favorite sweets and the bouquet of pink peonies.

"For you," he couldn't help but delight in her slight smile as she took out one macaroon and plopped it into her mouth and then tucked the rest of them away.

She kissed him on the cheek, "Thank you, this date has been…"

He cut her off, "Don't speak to soon, the night has only just started."

"Is that so?"

"Indeed," he rolled down the separating window, "Arthur, to the roof overlooking the skyline, you know the one."

"I should have known this couldn't be a date with Chuck Bass if it didn't include a portion involving a roof," she nudged him.

The comment didn't faze him, even he recognized that his love for roofs was rather characteristic, if not stereotypical, "There will be more waiting there than just the roof," and then he added smoothly, "And of course, this also couldn't be a date fit for Blair Waldorf if it didn't involve a slight tribute to the city."

She laughed a little and gazed out the window, "That is true, I do love New York."

"And I do love y—roofs." What was that? Pull it together, Bass.

Blair gave him a quizzical look but then shrugged it off, "We should both enjoy ourselves then."

He quickly averted this awkwardness developing any further by kissing her, "How could I not when I'm with you?"

"You do realize those kinds of lines don't work with me as they do your other women," she added that last part in disgust.

"Of course, your tastes are far superior," and then added slyly, "in every aspect."

They arrived at the roof overlooking the skyline where they had stood only weeks ago at her 17th birthday party. Blair smiled as she realized it was the place where Chuck had first admitted to actually liking her, but then frowned only a little as she remembered her initial response. However, to be fair, she had been justified at the time. He was Chuck Bass, after all.

"A lot has happened here," she said more to herself than him.

He replied anyways, "Indeed, which is why I thought it was a proper choice."

"It certainly is, I suppose, you actually really thought about all of this…"

"How could I not?"

She gave a half-hearted smile, "I'm sorry for what I said that night, I mean…at first."

He had to think about it a moment, in truth, all he could clearly remember was the beautiful ending of that night, "There's no need to apologize, that night turned out perfect in the end."

She laughed in a reminiscing tone, "I suppose it did, it does happen to be one of my favorite birthday celebrations."

"It also happens to be my favorite birthday party of yours that I've attended to this date, which is why I thought it fitting that it deserved a little continuation…"

"What do you mean?"

He examined her necklace, thinking for a moment how perfect it was that she had actually worn it, "That necklace, as I said, does deserve to be seen on someone worthy of its beauty, and I couldn't help but think that the bracelet did as well…," he pulled the box out of his pocket and opened it. Each and every diamond that it was made of shimmered even in the night.

Blair stared down at it, not reaching out for it quite yet, "Chuck…you didn't have to…it's…"

He kissed her forehead, "But I did," and he grabbed her hand and fastened the bracelet on her wrist anyways and watched as she examined the new piece of jewelry on her hand. It was undeniable that Blair had expensive taste, but her reactions had always been worth it. Not to mention the fact that shiny things did excite her in ways that always seemed to pay off later.

She grabbed his hand in hers this time as they walked to the edge of the roof to obtain a better view of the skyline, "Thank you, Chuck."

He only smiled and they stood in silence as they viewed the city where everything had happened. However, the silence was a comfortable one and they both felt at ease in the presence of one another. They both thought about how this city had held the club where everything had changed, the street and the limo where they had slept together for the first time, the hotel, her house, the building where cotillion was held and they had danced if only for a moment; the list went on and on. This city held everything that had held them at one point. Perhaps that had become the new reason why each of them both loved New York so incredibly much. It was not because they enjoyed the places, but rather because they enjoyed each other.

He turned to look at Blair and he didn't stop himself, "Blair, I…"

It was as if she knew what he was going to say already, "I know, I do too…"

He hated to admit it, but he was thankful she had stopped him, "Perhaps…"

"We still have a while to just enjoy each other," she tightened her grasp around his hand, and then added, "In fact, why don't we go back to your hotel and start right now?"

That of course, was an offer that he couldn't refuse. Even though he hadn't told her aloud that he loved her, he was comforted in the fact that in its place remained the mutual understanding. He would tell her one day, but for now, who was he to deny a good time?

**A/N: This concludes the story. I hope you enjoyed it. I'm probably going to be writing more one-shots from now on. (Of course, many with Chuck/Blair) So, if you'd be interested in those, please follow me. I thank you all for your continued support, it means so incredibly much! **

**As always, any comments and/or suggestions are highly appreciated. Both on this chapter and the story as a whole! Thank you for reading! You are all fantastic! **

**p.s.: I ended up writing this in an airport as I was waiting for a plane…so I hope the quality wasn't affected too much by the short amount of time I had to write it.**


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